Rhodium-catalyzed conversion of furans to highly functionalized pyrroles

Journal of the American Chemical Society

Volumn 135, Issue 12, 2013, Pages 4716-4718

  Parr, Brendan T ^a   Green, Samantha A ^a   Davies, Huw M L ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONALIZED; HEMIAMINALS; RHODIUM-CATALYZED; RING OPENING;

ORGANIC POLLUTANTS; RHODIUM;

AROMATIC COMPOUNDS;

CARBENE; FURAN DERIVATIVE; PYRROLE DERIVATIVE; RHODIUM; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COPE REARRANGEMENT; CYCLOPROPANATION; RING OPENING; THIN LAYER CHROMATOGRAPHY;

CATALYSIS; FURANS; IMINES; METHANE; PYRROLES; RHODIUM;

EID: 84875727243     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja401386z     Document Type: Article

References (32)

1. Kathiravan, M. K.; Salake, A. B.; Chothe, A. S.; Dudhe, P. B.; Watode, R. P.; Mukta, M. S.; Gadhwe, S. Bioorg. Med. Chem. 2012, 20, 5678
2. Heugebaert, T. S. A.; Roman, B. I.; Stevens, C. V. Chem. Soc. Rev. 2012, 41, 5626
3. Bauer, I.; Knöelker, H.-J. In Topics in Current Chemistry Alkaloid Synthesis; Knöelker, H.-J., Ed.;; Springer: Heidelberg, Germany, 2012; Vol. 309, pp 203-253.
4. Omastova, M.; Micusik, M. Chem. Pap. 2012, 66, 392
5. Hofmann, N. R. Plant Cell 2011, 23, 4167
6. Russel, J. S.; Pelkey, E. R.; Greger, J. G. Prog. Heterocycl. Chem. 2011, 23, 155
7. Bergman, J.; Janosik, T. In Modern Heterocyclic Chemistry; Alvarez-Builla, J.; Vaquero, J. J.; Barluenga, J., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2011; Vol. 1, pp 269-376.
8. Mal, D.; Shome, B.; Dinda, B. K. In Heterocycles in Natural Product Synthesis; Majumdar, K. C.; Chattopadhyay, S. K., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2011; Vol. 1, pp 187-222.
9. Humenny, W. J.; Kyriacou, P.; Sapeta, K.; Karadeolian, A.; Kerr, M. A. Angew. Chem., Int. Ed. 2012, 51, 11088
10. Narayan, R.; Froehlich, R.; Wuerthwein, E.-U. J. Org. Chem. 2012, 77, 1868
11. Chen, F.; Shen, T.; Cui, Y.; Jiao, N. Org. Lett. 2012, 14, 4926
12. Ryabchuk, P.; Rubina, M.; Xu, J.; Rubin, M. Org. Lett. 2012, 14, 1752
13. Xinxin, X.; Xianxiu, X.; Park, C.-M. Chem. Commun. 2012, 48, 3996
14. Geng, W.; Zhang, W.-X.; Hao, W.; Xi, Z. J. Am. Chem. Soc. 2012, 134, 20230
15. Schultz, E. E.; Sarpong, R. J. Am. Chem. Soc. 2013, submitted.
16. Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861
17. Davies, H. M. L.; Morton, D. Science of Synthesis, Stereoselective Synthesis; De Vries, J. G.; Molander, G. A.; Evans, A. P., Eds.; 2011; Vol. 3, p 513.
18. Chuprakov, S.; Gevorgyan, V. Org. Lett. 2007, 9, 4463
19. Chuprakov, S.; Hwang, F. W.; Gevorgyan, V. Angew. Chem., Int. Ed. 2007, 46, 4757
20. Horneff, T.; Chuprakov, S.; Chernyak, N.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972
21. Gulevich, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2013, 52, 1371
22. Chuprakov, S.; Kwok, S. W.; Zhang, L.; Lercher, L.; Fokin, V. V. J. Am. Chem. Soc. 2009, 131, 18034
23. Grimster, N.; Zhang, L.; Fokin, V. V. J. Am. Chem. Soc. 2010, 132, 2510
24. Chuprakov, S.; Malik, J. A.; Zibinsky, M.; Fokin, V. V. J. Am. Chem. Soc. 2011, 133, 10352
25. Selander, N.; Worrell, B. T.; Chuprakov, S.; Velaparthi, S.; Fokin, V. V. J. Am. Chem. Soc. 2012, 134, 14670
26. Zibinsky, M.; Fokin, V. V. Angew. Chem., Int. Ed. 2013, 52, 1507
27. Alford, J. S.; Davies, H. M. L. Org. Lett. 2012, 14, 6020
28. Davies, H. M. L.; Bruzinski, P. R.; Fall, M. J. Tetrahedron Lett. 1996, 37, 4133
29. Davies, H. M. L.; Hedley, S. J. Chem. Soc. Rev. 2007, 36, 1109
30. Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897
31. Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696
32. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774